Organic electroluminescent materials and devices

Abstract

This invention relates to compounds containing heterocycles or azaheterocycles and phenylene or azaphenylene wherein at least one ring is a five-membered ring. These novel compounds are useful as host materials for phosphorescent electroluminescent devices.

We claim: 
     
       1. A compound having Formula I: 
       
         
           
           
               
               
           
         
         wherein rings A to D are each independently a five- or six-membered carbocyclic or heterocyclic ring; 
         wherein at least one of rings A to D is a five-membered aromatic ring which is not triazole; 
         wherein at least one of rings A to D is a six-membered ring; 
         wherein rings A to D are each optionally substituted by a substituent selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
         wherein at least one of rings A to D is substituted by a substituent selected from the group consisting of aryl and heteroaryl, wherein said aryl or heteroaryl may be further substituted by a substituent selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and 
         wherein any adjacent substituents are optionally joined or fused to form a ring; 
         provided that when any of rings A to D is a five membered ring, then two adjacent substituents on the 5-membered ring are not joined or fused to form a ring; and 
         provided that when any of rings A to D is a six-membered ring, then two adjacent substituents on the 6-membered ring are not joined or fused to form a heterocyclic non-aromatic ring. 
       
     
     
       2. The compound of  claim 1 , wherein ring A to D are each optionally substituted by a substituent selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof. 
     
     
       3. The compound of  claim 1 , wherein rings A to D are aromatic rings. 
     
     
       4. The compound of  claim 1 , wherein one of rings A to D is a 5-membered ring and the remaining rings are 6-membered rings. 
     
     
       5. The compound of  claim 1 , wherein two of rings A to D are 5-membered rings and the remaining rings are 6-membered rings. 
     
     
       6. The compound of  claim 1 , wherein one of rings A to D is a 6-membered ring and the remaining rings are 5-membered rings. 
     
     
       7. The compound of  claim 1 , wherein rings A and B are 5-membered rings, and rings C and D are 6-membered rings. 
     
     
       8. The compound of  claim 1 , wherein rings A and D are 5-membered rings, and rings B and C are 6-membered rings. 
     
     
       9. The compound of  claim 1 , wherein when one or more of rings A to D are 5-membered rings, the 5-membered rings are selected from the group consisting of imidazole, furan, thiophene, pyrrole, oxazole, thiazole, pyrazole, isoxazole, isothiazole, oxadiazole, and thiadiazole. 
     
     
       10. The compound of  claim 1 , wherein when one or more of rings A to D are 6-membered rings, the 6-membered rings are selected from the group consisting of benzene, pyridine, pyridazine, pyrimidine, pyrazine, and triazine. 
     
     
       11. The compound of  claim 1 , wherein at least one of rings A to D is selected from the group consisting of pyridine, pyridazine, pyrimidine, pyrazine, and triazine. 
     
     
       12. The compound of  claim 1 , wherein at least one of rings A to D is substituted by a substituent selected from the group consisting of carbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, triphenylene, azatetraphenylene, tetraphenylene, silyltetraphenylene, fluorene, azacarbazole, azadibenzofuran, azadibenzoselenophene, azatriphenylene, xanthene, phenoxasilin, 9,9-dimethylxanthene, 10,10-dimethylphenoxasilin, thioxanthene, phenothiasilin, 9,9-dimethylthioxanthene, 10,10-dimethylphenothiasilin, 9,9′-spirobisxanthene, 9,9′-spirobisthioxanthene, 10,10′-spirobiphenoxasilin, 10,10′-spirobiphenothiasilin, benzimidazole[2,1-b]benzothiazole, 5H-benzimidazo[1,2-a]benzimidazole, benzimidazo[2,1-Mbenzoxazole, azabenzimidazole[2,1-b]benzothiazole, aza5H-benzimidazo[1,2-a]benzimidazole, azabenzimidazo[2,1-Mbenzoxazole, and azafluorene. 
     
     
       13. A compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       14. An organic light emitting device (OLED) comprising:
 an anode; 
 a cathode; and 
 an organic layer, disposed between the anode and the cathode, comprising a compound of  claim 13 . 
 
     
     
       15. A consumer product comprising the OLED of  claim 14 . 
     
     
       16. An organic light emitting device (OLED) comprising:
 an anode; 
 a cathode; and 
 an organic layer, disposed between the anode and the cathode, comprising a compound having Formula I: 
 
       
         
           
           
               
               
           
         
         wherein rings A to D are each independently a five- or six-membered carbocyclic or heterocyclic ring; 
         wherein at least one of rings A to D is a five-membered ring which is not triazole; 
         wherein rings A to D are each optionally substituted by a substituent selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and 
         wherein any adjacent substituents are optionally joined or fused to form a ring; 
         provided that when any of rings A to D is a five membered ring, then two adjacent substituents on the 5-membered ring are not joined or fused to form a ring. 
       
     
     
       17. The OLED of  claim 16 , wherein the organic layer is an emissive layer and the compound of Formula I is a host. 
     
     
       18. The OLED of  claim 16 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein each Y 1  to Y 13  are independently selected from the group consisting of carbon and nitrogen; 
         wherein Y 1  is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═0, S═0, SO 2 , CR e R f RR, SiR e R f , and GeR e R f ; 
         wherein R e  and R f  are optionally fused or joined to form a ring; 
         wherein each R a , R b , R e , and R d  may independently represent from mono substitution to the maximum possible number of substitution, or no substitution; 
         wherein each R a , R b , R e , R d , R e , and R f  is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof; and 
         wherein any two adjacent substituents of R a , R b , R c , and R d  are optionally fused or joined to form a ring or form a multidentate ligand. 
       
     
     
       19. The OLED of  claim 16 , wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer, or the organic layer is a transporting layer and the compound of Formula I is a transporting material in the organic layer. 
     
     
       20. A consumer product comprising the OLED of  claim 16 . 
     
     
       21. The consumer product of  claim 20 , wherein the consumer product is selected from the group consisting of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, and a sign.